


Dammit Cas with the awkward questions!

by sp00kyskeletons



Category: Supernatural
Genre: Basically Porn, Bottom Castiel, Fingering, First Time, I'm bad at tagging guys, M/M, Smut, Top Dean, Virgin Castiel, like half of this is smut
Language: English
Status: Completed
Published: 2016-09-07
Updated: 2016-09-07
Packaged: 2018-08-13 14:43:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,979
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7980361
Author URL: https://archiveofourown.org/users/sp00kyskeletons/pseuds/sp00kyskeletons
Summary: <blockquote class="userstuff">
              <p>Cas could be infuriating. And by that I mean his lack of understanding with humans and asking awkward questions.</p><p>He had no idea what was, and wasn't, appropriate to ask. Like, at all.</p><p>For instance, when he decided to ask Dean about what Tentacle Porn was, brilliant. And while Dean does not get flustered very easily, he did this time. You just don't ask a dude about these sorts of questions. Thank fuck Sam wasn’t in the room or that would have made or even more awkward time.</p>
            </blockquote>





	Dammit Cas with the awkward questions!

**Author's Note:**

> Dunno if any of you are reading my previous, current work in progress with cat Castiel. Either way, I found it a bit triggering but also an outlet for my feelings as I have had a pretty unfortunate incident. For now I'll be taking a break for a couple of days before adding another chapter or two, apologies.
> 
> Either way, enjoy this smut lolol.

Cas could be infuriating. And by that I mean his lack of understanding with humans and asking awkward questions.

He had no idea what was, and wasn't, appropriate to ask. Like, at all.

For instance, when he decided to ask Dean about what Tentacle Porn was, brilliant. And while Dean does not get flustered very easily, he did this time. You just don't ask a dude about these sorts of questions. Thank fuck Sam wasn’t in the room or that would have made an even more awkward time.

Once Cas was satisfied with Dean's answer he seems to wonder off through the bunker, possibly going to ask Sam a difficult question. And Dean headed towards the shower to rub one out.

His feelings towards the angel had been mixed as of recent. He liked the guy, and he found his mind wandering off into fantasies. He could quite easily get himself off over the thought of Cas wrapping his perfect pink lips around his cock, or riding Dean to orgasm. Honestly, he wanted to touch that perky ass of his and to tease his fingers around what he imagined to be a beautifully tight hole. He wanted to find what made the Angel snap and what he enjoyed, he wanted to see how Cas looked during orgasm. He wanted to push him over the edge.

Dean very often found himself thinking these thoughts, but then would often be disgusted with himself. He wasn't gay, he never would be. Why did he think this? What was wrong with him? He had only found an interest in women until this fucker named Castiel waltzed his ass in and became apart of his life.

Sitting here thinking about Cas wasn't going to provide him with any answers to their latest case. Better get on his laptop and start researching.

*** * ***

Turns out the case wasn't as simple as they thought. One part of it was some children who had stumbled into witchcraft, they had no idea what they were doing. They just thought it was fun and games and didn't realize the consequences of turning people into cats, or dogs, or whatever the hell else they decided would be a good laugh. They honestly looked incredibly upset and apologised profusely, they didn't realize their actions would cause major issues. Turning somebody into a bug meant that if they got killed in bug form, they would be killed in human form too. 

The kids were only around 11 or 12, they just wanted to have some fun. One of the siblings offered Sam and Dean a cookie, obviously not knowing how else to apologise. The brothers accepted the apology and Sam gave the siblings the hug, showing that they weren't mad. However, if they did cause trouble again, there would be serious consequences.

But that was just one side of the story, as it seemed that there was a dead pissed off witch roaming the area. It generally killed anything that moved or got to close to the house where it took residence. Something simple turned into Dean almost being killed and having a dislocated shoulder. Fun huh?  
Heading back to the bunker was a quiet and smooth journey. Sam was driving due to Dean's fucked up shoulder and he was glad the road was smooth. Any movement seriously hurt like heck.

Pulling up and heading into the bunker, Sam looked over at his brother.  
"Dude, you alright?"  
"Do I look like I'm alright? My shoulder is fucking busted and it hurts like fuck!" Sam frowned slightly. He didn't like it when his brother was in pain, and Cas didn't seem to be around to heal him up. Silently sending a prayer to Castiel, he was hoping he would pick up and could spare a few moments to come down and heal his brother.  
Sam knew there was something going on between Cas and Dean. Since Cas had been too busy to come by so often due to the war in heaven, Dean’s mood had gotten worse. He was generally quite depressed, drinking more often. Sam sighed, all he wanted was his brother to be somewhat happy again.

Sam was snapped from his thoughts when he was greeted by a ruffling of feathers. Cas. Sam sighed with relief, hoping that he would be able to heal dean.  
“I came as soon as I could Sam. What seems to be the problem?”  
“Dean pretty much screwed up his shoulder on the hunt, I was hoping you could heal him possibly? I know he’s in an awful lot of pain and refused to let me touch it.” Cas nodded his head, processing the information,  
“And well, I think Dean really misses you Cas. Don’t say I said this because he’ll cut my dick off for sure, but he’s been more depressed since you’ve had less time to come by and just hang out. I don’t know what’s going on between you, if anything. But he’s been pretty down… I dunno, if you could just pop in every now and again, or whenever your free. I think it could really cheer him up.” Castiel once again nodded his head, taking on board the information of what Sam was telling him.  
“I will try to come by more often, to see Dean and you, Sam. I do enjoy your company; I just have been incredibly busy.” Cas replied, before looking around to see if he could see Dean anywhere. Locating Dean in his bedroom, he headed off.

Castiel knocked on Dean’s door.  
“Dean, may I come in?”  
“Yeah okay whatever” Came a forlorn voice from the other side of the door. Cas entered, seeing Dean hunched over on the bed with already several empty bottles of alcohol surrounding him. Softly sighing and shaking his head, he walked over towards Dean and pressed two fingers to his forehead, healing his shoulder and any other bruises on his body. 

“Dean, what’s the matter? You’re not… you. You’re sad.” Cas stated simply. All Dean did was take another swig of his alcohol, whatever it was, he didn’t care and didn’t reply. He wasn’t in the mood for a long conversation, if anything, he just wants to drown his problems by being drunk. 

Cas frowned, he didn’t like to see Dean upset. While angels didn’t feel the same emotions as humans, Castiel had been having thoughts about Dean as of recent. They were impure thoughts; thoughts angels were told they were not allowed to have. He wanted to kiss Dean, to have Dean fuck him, to have Dean kiss every inch of his body. He wanted to feel Dean’s hands all over him, he wanted to please Dean by getting on his knees and sucking him off.

While Cas was a complete virgin, he had watched porn and videos on how to suck a guy off or how to get the most pleasure out of sex. It made his vessel excited and caused a strain in his boxers. 

Maybe Sam was right, Dean was rarely like this when Cas had more time to stop by. Maybe just to joke around, watch a movie, do research. Sam had even suggested one day they could introduce Cas to board games, and Cas decided he did quite like the idea of that.

But now? Now that he doesn’t have the time to come by so often, if at all? Dean seemed sad. He didn’t pray to Cas anymore. If it was anybody, it was Sam asking for help and asking for Castiel to come down to help his brother.

Cas sucked in a breath, he wanted to kiss Dean, he wanted to know what his lips tasted like.

“Dean?”  
“Yeah Cas?”  
“May I kiss you?” Dean stuttered, swallowing his beer hard. Did Cas feel the same, did he want to make out with Dean? Was he even awake right now or was this a dream? Dean honestly didn’t know, but he didn’t waste much more time before standing up and connecting his lips to Cas’s. Sparks went off, he could feel butterflies in his stomach. It felt so right. So good.

Dean broke away and looked into Castiel’s eyes, searching for any signs of regret, and finding none. So he decided that he liked it so much he would do it again. This time entering his tongue into Cas’s mouth, exploring all he had to offer. He tasted wonderful and his lips felt amazing.

Suddenly Castiel shifted, and Dean was very aware of the erection pressing against him, but also his own erection. The shorter man’s hands where currently on Dean’s hips, looking up at him, waiting for Dean to make the next move. For Dean to take control. For Dean to give orders. The thought of that caused Dean to shiver and to let out a small, low growl.

“Cas, where would you like this to go? Where do you want this to end up?” Cas seemed to be looking for an answer and gripped Dean’s hips a little harder.  
“I’d like you to fuck me Dean” Came the final reply, before returning his eyes up to Dean, silent pleads to take care of him and to make him feel good. And oh was Dean going to do just that.

“Then strip, then on the bed with your ass in the air.”

He watched Cas let go and remove his clothes, somewhat hastily as if he thought Dean would change his mind if he wasn’t quick enough. It was quite a sight to see, if it wasn’t for the control he had he would be on top of Cas right now. But even so, it was difficult not too.

Cas laid on the bed, finding a comfortable position and put his ass up in the air. He looked over at Dean, making eye contact before wiggling his ass in the air. Dean once again let out a growl at the sight, palming himself through his jeans. He didn’t think he could get this hard, nor could he get his aroused. No amount of busty Asian Beauties had ever caused him to feel the way he did now.

Removing his shirt and jeans to alleviate some of the pressure in between the legs. Dean walked over to the nightstand and got some lube out that he always kept, because he sometimes needed to use it himself. Dean ran his hands over the angels back down to his ass, squeezing it slightly. He watched as the man shivered, pushing his ass into Dean’s hand, causing a slight smirk to fall onto his face.

Dean placed himself behind Cas, and generously lubed up two fingers. He circled his index finger around the puckered muscle, watching the angel twitch and the muscle respond under his fingers. Dean continued doing this, pressing slightly but never entering until a broken plea broke the silence.  
“Dean please.” A smirk came onto Dean’s lips, he wanted to tease Cas and hear him beg for it.

“Mm, show me how much you want it, princess.” Cas whined at the pet name and pushed back against Dean’s finger. He wanted it inside of him, he wanted some type of small release or he was going to go insane.  
“Please please please Dean, fuck me on your fingers, prepare me for your massive cock. Please please please Dean, I really need you” Came the broken and breathy words off of the angel’s lips.  
Smiling Dean pushed a finger inside and Cas tensed up, before trying to relax. Dean hummed, slowly moving his digit in and out, allowing Cas to get used to the sensation of something inside of him. 

After a few moments Dean added a second finger, gently scissoring, stretching out the tight ring of muscle. A small whimper came from the angel.  
“You okay Cas?” Cas nodded his head.  
“Feels good... But a little painful” Dean hummed, he hadn’t ever bottomed but he had used toys to hit his prostate and remembered how good that felt. But he also remembered the first time of opening himself up was a little painful.

“It will hurt, but just try to keep yourself relaxed” Dean told him, moving the two digits around trying to find the sweet spot that would distract Cas from the slight burn from having something invade him. He guessed he found it when a gasp came from the short man’s lips and his body jerked involuntarily. A smirk came onto Dean’s face.

He coated another finger in lube, he added the extra finger and used his free hand to fondle Cas’s balls, while also lightly tickling his prostate every now and again. The needy little gasps came from the angel’s lips, and when he began to push back into Dean, Dean knew he was ready to take his dick.

Dean removed his fingers earning a whimper from Cas, and he looked around at Dean to see where he was and why he had stopped. His face was flushed red, and some hair had stuck to his forehead. Dean hummed and coated his cock generously in lube, this was Cas’s first time and he wanted to make him feel good and for it not to hurt.

“Deeeeeeeeeeean” Came the needy whine. If you had told Dean all those years ago that he’d have a needy angel of the lord in front of him begging to be fucked, he would have looked at you like you had grown another head. But right now he had a powerful angel of the lord in front of him, opening up and trusting Dean. Allowing Dean to tease him, to touch him. With the strength of him Cas could easily throw Dean onto the bed and ride him, or take control. But instead he allowed himself to feel vulnerable, to be submissive. And Dean was the man trusted to do this.

“On your back princess, I wanna see your pretty face when I fuck you.” Upon the request Castiel quickly moved onto his back. Dean chuckled as Cas clearly had little idea what he was doing nor that Dean couldn’t fuck him unless his legs were spread.  
“Cas, you need to spread your legs or I can’t get to that pretty pink hole of yours.” The angel seemed to blush at something so simple, at something he forgot. So Cas moved his legs apart, and Dean smiled. 

Manhandling Cas’s legs to go around his hips, Dean lined himself up to the angel’s hole. He pushed in slowly, all while kissing the man. While the push in was slow, the kiss was needy and sloppy. But neither of them really cared. All they cared about was one another and what was happening right now.

When Cas began getting fidgety and trying to get Dean to fuck him, he took that as his cue to start moving. He went slow at first, watching the angel’s face for any sign of pain or regret of what they were doing. But the blue eyes, that were mainly black due to his lust filled eyes, just looked up at Dean with utter trust.

Cas was a complete virgin, but he knew how to get Dean to speed up the pace which is what he wanted. He had had enough teasing, he wanted some sort of release. He was feeling desperate. So with some thought, he tried his hand at teasing.

“Deaaaaaaan… When I asked you to fuck me, I didn’t mean like I was a fragile baby.” He saw Dean’s eyes get darker, a low growl escaping his throat.  
“Bet you can’t fuck me any harder…” Castiel said with a smirk while keeping eye contact with Dean.  
“Bet you can’t get me to cum screaming…”

Riling Dean up was one of the best decisions he could have decided to do. Dean’s eyes got impossibly dark, and picked up his pace. He was slamming into Cas, skin slapping and his balls slapping against Cas’s perky little ass. Dean shifted his position, trying to find the sweet spot inside of the angel. And when a sudden squeal came off of the angel’s lips, he knew he had the right spot.

Dean smirked.  
“Mm yeah, that’s right baby. Scream, let them know who’s fucking you good like this”

Cas could feel himself getting close, a heat pooling up in his belly and his balls tightening. He couldn’t hold back the moans anymore, and let himself go. Let himself be loud. Which seemed to cause Dean to go deeper and harder.

“D-Dean… Gonna…” Cas didn’t get the chance to finish his sentence before he came all over himself in long spurts, all while screaming Dean’s name.

With the impossible tightness of Cas around him getting even tighter, convulsing making the pleasure too much to handle, Dean came buried deep inside the angel’s ass. Milking him for all he had to offer.

Dean pulled out and flopped next to Cas, bringing him close and holding him. All that could be heard was their breaths in sync. Cas used his mojo to clean the cum off of his stomach, but didn’t bother to do anything else. Instead, he rolled over so he was facing Dean and pressed kisses to his jaw. Dean smiled, feeling complete for once.

“Dean…” Cas said, sounding unsure.  
“Yes?”  
“Where does this leave us… What does it make us?” Cas questioned. Dean sucked in a breath. Not sure how to answer. He knew that he would like to be Cas’s boyfriend, but what did Cas want?  
“I’d like it to make us boyfriends, in a relationship, y’know?” The angel nodded his head, thinking about what Dean said.  
“I’d like that.” He said, looking up at Dean, deciding to press his lips to the taller man. Dean smiled into the kiss.  
“Good, my angel boyfriend” Dean mumbled against Cas’s lips.

He could deal with Sam tomorrow.


End file.
